SciELO - Scientific Electronic Library Online

 
vol.63Hydrogen bonding patterns in a series of 3-spirocyclic oxindolesSynthesis of (S)-3-aminoethyl-1,2,3,4-tetrahydroisoquinoline (TIQ-diamine) via the Mitsunobu protocol author indexsubject indexarticles search
Home Pagealphabetic serial listing  

Services on Demand

Article

Indicators

Related links

  • On index processCited by Google
  • On index processSimilars in Google

Share


South African Journal of Chemistry

On-line version ISSN 1996-840X
Print version ISSN 0379-4350

S.Afr.j.chem. (Online) vol.63  Durban  2010

 

RESEARCH ARTICLE

 

Simple, efficient and green synthesis of oximes under ultrasound irradiation

 

 

A. Khoramabadi-Zad*; M. Azadmanesh; A. Rezaee

Faculty of Chemistry, Bu-Ali Sina University, Hamadan 65174, Iran

 

 


ABSTRACT

The condensation of aldehydes and ketones with hydroxylamine hydrochloride gives oximes in 81-95 % yields in water and EtOH under ultrasound irradiation. Compared to conventional methods, the main advantages of the present procedure are milder reaction conditions, shorter reaction times and higher yields.

Keywords: Condensation, oxime, ultrasonication, aldehydes, ketones


 

 

Full text available only in PDF format.

 

Acknowledgement

We gratefully acknowledge the support of this work by Bu-Ali Sina University Research Council.

 

References

1 (a) T.J. Mason and D. Peters, Practical Sonochemistry 2nd edn., Ellis Horwood, London, 2002.         [ Links ] (b) J.L. Luche, Synthetic Organic Sonochemistry, Plenum Press, New York, 1998.         [ Links ] (c) J.T. Li, Y.J. Bian, H.J. Zang, T.S. Li, Synth. Commun. 2002, 32, 547-551.         [ Links ] (d) J.T. Li, W.Z. Yang, S.X. Wang, S.H. Li and T.S. Li, Ultrason. Sonochem. 2002, 9, 237-239.         [ Links ]

2 F.M. Herman, Encyclopedia of Polymer Science and Technology, Vol. 12, 3rd edn., John Wiley & Sons Inc., New York, NY, USA, 2004.         [ Links ]

3 (a) H.M.S. Kumar, T.P. Reddy and J.S. Yadav, Synthesis 1999, 586-587.         [ Links ] (b) B. Das, P. Madhusudhan and B. Venkataiah, Synlett. 2000, 1599-1600.         [ Links ]

4 (a) D.C. Iffland and T.F. Yen, J. Am. Chem. Soc. 1954, 76, 4083-4085.         [ Links ] (b) P.R. Dave, F. Forohar, T. Axenrod, K.K. Das, L. Qi, C. Watnick and H. Yazdekhasti, J. Org. Chem. 1996, 61, 8897-8903.         [ Links ] (c) F.P. Ballistreni, E. Barbuzzi, G.A. Tomaselli and R.M. Toscano, Synlett. 1996, 1093-1094.         [ Links ]

5 M.E. Xenikaki, X.N. Stamplos, T.A. Charalambis and C.C. Karapostolon, Tetrahedron 1997, 53, 747-758.         [ Links ]

6 (a) S. Sasatani, T. Miyazak, K. Maruoka and H. Yamamoto, Tetrahedron Lett. 1983, 24, 4711^712.         [ Links ] (b) S. Negi, M. Matsukura, M. Mizuno and K. Miyake, Synthesis 1996, 991-996.         [ Links ]

7 M. Tordeux, K. Boumizane and C. Wakselman, J. Org. Chem. 1993, 58, 1939-1940.         [ Links ]

8 H.W. Shih and W.C. Cheng, Tetrahedron Lett. 2008, 49, 1008-1011.         [ Links ]

9 M. Lauer, B. Zipperer and N. Goetz, European Patent. EP 409077, 1991.         [ Links ]

10 R. Benoit, H. Sauter and R. Kirstgen, European Patent. EP 498188, 1992.         [ Links ]

11 U. Misslitz, N. Meyer and J. Kast, Ger. Offen. DE 4018623, 1991.         [ Links ]

12 K. Lazonova, G.Vasilev and V. Kalcheva, Dokl. Bulg. Akad. Nauk. 1992, 44, 115-118.         [ Links ]

13 T.W. Greene and P.G.M. Wuts, Protective Groups in Organic Synthesis, 4th edn., John Wiley & Sons Inc., New York, NY, USA, 2006.         [ Links ]

14 M. Kizil and J.A. Murphy, Tetrahedron 1997, 53, 16847-16858.         [ Links ]

15 F.D. Aparicio, J.M. De Los Santos and E. Rodriguez, Tetrahedron 1998, 54, 599-614.         [ Links ]

16 (a) A.K. Mitra, A. De and N. Karchaudhuri, J. Indian Chem. Soc. 1999, 76, 218-219.         [ Links ] (b) G.L. Kad, M. Bhandari, J. Kaur, R. Rathee andJ. Singh, Green Chem. 2001, 3, 275-277.         [ Links ]

17 H. Sharghi and M. Hosseini Sarvari, Synlett. 2001, 1, 99-101.         [ Links ]

18 J.J. Xia and G.W. Wang, Molecules 2007, 12, 231-236.         [ Links ]

19 J.T. Li, X.L. Li and T.S. Li, Ultrason. Sonochem. 2006, 13, 200-202.         [ Links ]

20 I. Mohammadpoor-Baltork, A.R. Hajipour and R. Haddadi, J. Chem. Res. 1999, 102-103.         [ Links ]

21 J. Buckingham, J.I.G. Cadogan, R.A. Raphael and C.W. Rees, eds, Dictionary ofOrganic Compounds, 5th edn., Chapman & Hall, New York, 1982.         [ Links ]

22 http://riodb01.ibase.aist.go.jp/sdbs/cgi-bin/cre_index.cgi?lang=eng        [ Links ]

23 S. Dayagi and Y. Degani, The Chemistry of Carbon-Nitrogen Double Bond, (S. Patai, ed.), Interscience, London, 1970.         [ Links ]

24 J. R. Hwu and S. C. Tsay, Tetrahedron 1990, 46, 7413-7428.         [ Links ]

25 (a) D. Albanese, D. Landini and M. Penso, Synthesis 1990,333-336.         [ Links ] (b) N. Zou and B. Jiang, J. Comb. Chem. 2000, 2, 6-7.         [ Links ]

26 T. Okamoto, K. Kobayashi, S. Oka and S. Tanimoto, J. Org. Chem. 1988, 53, 4897-4901.         [ Links ]

 

 

Received 2 August 2010
Revised 19 October
Accepted 1 November 2010

 

 

* To whom correspondence should be addressed. E-mail: khoram@gmail.com

Creative Commons License All the contents of this journal, except where otherwise noted, is licensed under a Creative Commons Attribution License